Curable silicone composition and applications and uses thereof

Abstract

A curable composition comprising (A) an organopolysiloxane comprising a curable functional group; and (B) a silicone-free, organic material comprising a reactive functional group. The curable composition exhibits high refractive index and optical clarity. The curable composition can be used to prepare a cured material that exhibits high refractive index, optical clarity, crack resistance, and low moisture vapor permeability.

What is claimed is: 
     
       1. A curable silicone composition comprising:
 (A) an organopolysiloxane with a formula: 
 
       
         
           
           
               
               
           
         
       
       where R 1  is a divalent organic group chosen from a C1-C20 divalent hydrocarbon, a C4-C20 branched divalent hydrocarbon, or a C4-C30 cyclic-containing hydrocarbon group; 
       R 2  is a curable functional group independently chosen from a vinyl, a vinyl-containing group, an unsaturated hydrocarbon, an unsaturated cyclic hydrocarbon, an acrylate, a methacrylate, a hydroxy, an alkoxy, and an epoxy; 
       R 3 -R 14  are independently chosen from hydrogen, a C1-C10 monovalent hydrocarbon group, a C6-C20 monovalent aromatic group, and a C4 to C30 monovalent saturated or unsaturated cycloalkyl group, siloxy group containing 1-20 silicon atoms; 
       x and z are independently 1-30; 
       y and w are independently 0-30; and 
       n is 1-30; and
 (B) a silicone-free organic material comprising a reactive functional group, wherein the silicone-free organic material (B) is chosen from an ethylenically unsaturated monomer, an ethylenically unsaturated aromatic compound, an ethylenically unsaturated acid, an ethylenically unsaturated anhydride, an acrylate, a methacrylate, an acrylamide, or a combination of two or more thereof. 
 
     
     
       2. The curable silicone composition of  claim 1 , wherein the silicone-free organic material (B) is chosen from an organic monomer comprising an olefinic functional group, an organic monomer comprising an acrylic functional group, an organic oligomer comprising an acrylic functional group, or a combination of two or more thereof. 
     
     
       3. The curable composition of  claim 2 , wherein the organic monomer comprising an olefinic functional group is chosen from a polyisobutene comprising an alkenyl functional group. 
     
     
       4. The curable composition of  claim 3 , wherein the polyisobutene is chosen from a vinyl terminated polyisobutene. 
     
     
       5. The curable composition of  claim 1 , wherein the organic monomer (B) is an organic monomer comprising an acrylic functional group chosen from a alkyl acrylate, an alkylene glycol acrylate, an epoxy acrylate, an alkoxylated epoxy acrylate, an alkoxy alkyl acrylate, an aryl acrylate, a urethane acrylate, an aminated acrylate, or a combination of two or more thereof. 
     
     
       6. The curable composition of  claim 5 , wherein the organic monomer comprising an acrylic functional group is chosen from 2-butoxyethyl acrylate, 2-butoxyethyl methacrylate, 2-ethoxyethyl acrylate, 2-ethoxyethyl methacrylate, 2-ethyl-2-adamanthyl acrylate, 2-ethyl-2-adamanthyl methacrylate, 2-hydroxyethyl acrylate, 2-methyl-2-adamanthyl acrylate, 2-methyl-2-adamanthyl methacrylate, benzyl acrylate, cyclohexyl acrylate, di(ethyleneglycol)ethylether acrylate, di(ethyleneglycol)ethylether methacrylate, di(ethylene glycol)methylether methacrylate, dicyclofentanyl acrylate, epoxy acrylate, ethylene glycol methyl ether acrylate, ethylene glycol phenyl ether acrylate, hydroxypropyl acrylate, isobornyl acrylate, methyl adamanthyl arcylate, neopentyl glycol benzoate acrylate, 2-hydroxymethyl methacrylate, adamanthyl methacrylate, alkyl methacrylate, benzyl methacrylate, cyclohexyl methacrylate, dicyclopentanyl methacrylate, epoxycyclohexylmethyl methacrylate, ethylene glycol phenyl ether methacrylate, hydroxylbutyl methacrylate, hydroxypropyl methacrylate, isobornyl methacrylate, glycydyl methacrylate, methyl adamanthyl methacrylate, methyl methacrylate, methyl glycydyl methacrylate, isobutyl acrylate, tert-butyl acrylate, lauryl acrylate, alkyl acrylate, 2-hydroxy acrylate, trimethoxybutyl acrylate, ethyl carbitol acrylate, phenoxyethyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 3-fluoroethyl acrylate, 4-fluoropropyl acrylate, and triethyl siloxyl ethyl acrylate, or a combination of two or more thereof. 
     
     
       7. The curable silicone composition of  claim 1 , wherein R 1  is chosen from a divalent group comprising a C4-C30 cyclic-containing hydrocarbon group chosen from a cyclobutyl group, cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a divalent group derived from 1,1-diethenyl cylcohexane; 1,3-diethenyl cylcohexane; bicyclo[2.2.1]-2,5-dienthenylheptane; 1,4-di-2-prope-1-nylcyclochexane; a spiro[5.5]-3,8-diethenylundecane; a1,3-diethenyladamantane; a vinyl norbornene; 3,9-divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane; or pinane, bornane, norpinane, norbornane, spiro[2.2]pentane, spiro[2.3]hexane, spiro[2.4]heptane, spiro[2.5]octane, spiro[3.3]heptane, spiro[3.4]octane, spiro[3.5]nonane, spiro[4.4]nonane, spiro[4.5]decane, spiro[5.5]undecane, bicyclo[1.1.0]butane, bicyclo[2.1.0]pentane, bicyclo[2.2.0]hexane, bicyclo[3.1.0]hexane, bicyclo[3.2.0]heptane, bicyclo[3.3.0]octane, bicyclo[4.1.0]heptane, bicyclo[4.2.0]octane, bicyclo[4.3.0]nonane, bicyclo[4.4.0]decane, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, bicyclo[3.2.2]nonane, bicyclo[3.3.1]nonane, bicyclo[3.3.2]decane, bicyclo[3.3.3]undecane, an adamantyl, tricyclo[5.2.1.0 2,6 ]decane tricyclo[4.3.1.1 2,5 ]undecane rings. 
     
     
       8. The curable silicone composition of  claim 1 , wherein R 2  is chosen from a C1-C20 hydrocarbon radical comprising a vinyl functional group, a monovalent C4-C20 branched hydrocarbon radical comprising a vinyl functional group, or a monovalent C4 to C30 cyclic hydrocarbon radical comprising a vinyl functional group. 
     
     
       9. The curable silicone composition of  claim 1 , wherein R 2  is of the formula X—R 16 — where X is the curable functional group chosen from a vinyl group (CH 2 ═CH 2 —), an unsaturated cyclic group, an unsaturated polycyclic group, and R 16  is a bond or a C1-C20 monovalent hydrocarbon radical. 
     
     
       10. The curable silicone composition of  claim 9 , wherein X is chosen from cyclopentene, cyclohexene, cyclooctene, pinene, bornene, norpinene, norbornene, spiro[2.2]pentene, spiro[2.3]hexene, spiro[2.4]heptene, spiro[2.5]octene, spiro[3.3]heptene, spiro[3.4]octene, spiro[3.5]nonene, spiro[4.4]nonene, spiro[4.5]decene, spiro[5.5]undecene, bicyclo[1.1.0]butene, bicyclo[2.1.0]pentene, bicyclo[2.2.0]hexene, bicyclo[3.1.0]hexene, bicyclo[3.2.0]heptene, bicyclo[3.3.0]octene, bicyclo[4.1.0]heptene, bicyclo[4.2.0]octene, bicyclo[4.3.0]nonene, bicyclo[4.4.0]decene, bicyclo[1.1.1]pentene, bicyclo[2.1.1]hexene, bicyclo[2.2.1]heptene, bicyclo[2.2.2]octene, bicyclo[3.1.1]heptene, bicyclo[3.2.1]octene, bicyclo[3.2.2]nonene, bicyclo[3.3.1]nonene, bicyclo[3.3.2]decene, bicyclo[3.3.3]undecene, an adamantene, tricyclo[5.2.1.0 2,6 ]decene, tricyclo[4.3.1.1 2,5 ]undecene rings, a limonene, a camphene, a limonene oxide, a vinyl cyclohexyl epoxide, a dicyclopentadiene, 5-ethylidene-2-norbornene, 2-vinyl adamantane, 2-methylene admantane, dicyclopentadiene, or (−)-beta-chamigrene, 4-vinyl cyclohexyl. 
     
     
       11. The curable silicone composition of  claim 1  further comprising (C) a cross-linker; (D) a reaction accelerating agent; (E) an inhibitor; and/or (F) one or more additives. 
     
     
       12. The curable silicone composition of  claim 11  comprising the cross-linker (C), wherein the cross-linkier is chosen from a silicone-containing compound comprising at least one —SiH group, at least one —SH group, a vinyl group, a vinyl-containing group, an unsaturated hydrocarbon, an unsaturated cyclic hydrocarbon, an acrylate, a methacrylate, a hydroxy, an alkoxy, an epoxy, or a combination of two or more thereof. 
     
     
       13. The curable silicone composition of  claim 11 , wherein the reaction accelerating agent is selected from a photoinitiator, a thermal initiator, a metal-containing catalyst, or a combination of two or more thereof. 
     
     
       14. The curable silicone composition of  claim 11 , wherein the inhibitor is selected from an an ethylenically unsaturated amide, an aromatically unsaturated amide, an acetylenic compound, an ethylenically unsaturated isocyanate, an olefinic siloxane, an unsaturated hydrocarbon diester, an unsaturated hydrocarbon mono-ester of an unsaturated acid, a conjugated or isolated ene-yne, a hydroperoxide, a ketone, a sulfoxide, an amine, a phosphine, a phosphite, a nitrite, a diaziridine, or a combination of two or more thereof. 
     
     
       15. The curable silicone composition of  claim 11 , wherein the additive is selected from an antioxidant, a thermal stabilizer, an adhesion promoter, a filler, a pigment, a dye, a filler treating agent, a plasticizer, a spacer, an extender, a biocide, a stabilizer, a flame retardant, a surface modifier, an anti-aging additive, a rheological additive, a corrosion inhibitor, a surfactant or a combination of two or more thereof. 
     
     
       16. The composition of  claim 15 , wherein the adhesion promoter is chosen from an amino silane, an epoxy silane, an isocyanurate silane, a mercapto silane, an imido silane, an anhydride silane, a carboxylate functionalized siloxane, or a combination of two or more thereof. 
     
     
       17. The curable silicone composition of  claim 1 , wherein the composition has a refractive index of from 1.40 to 1.60. 
     
     
       18. The curable silicone composition of  claim 1 , wherein the composition has a transparency of ≥95%. 
     
     
       19. The curable silicone composition of  claim 1 , wherein the composition has a MVTR of about 0.1 to about 15 g/m 2 ·day, and an O permeability of 10 −1  to 10 g/m 2 ·day. 
     
     
       20. A cured article formed from curing the composition of  claim 1 . 
     
     
       21. The cured article of  claim 20 , wherein the article has a refractive index of from 1.40 to 1.60; a transparency of ≥95%; a MVTR of about 0.1 to about 15 g/m 2 ·day, and an O permeability of 10 −1  to 10 g/m 2 ·day, or a combination of two or more thereof. 
     
     
       22. The cured article of  claim 20 , wherein the article is chosen from an encapsulant, an optical waveguide, a lens, a bonding material, an adhesive, an film or sheet, laminated film of sheet, a coating, a pressure sensitive adhesive, or a wound care patch. 
     
     
       23. The cured article of  claim 20 , wherein the article is chosen from an LED encapsulant, an optical waveguide, a optical lens, an optical bonding material, an optical adhesive, an optical film or sheet, laminated film of sheet, in electronic component or in combination with semiconductor device. 
     
     
       24. A personal care composition comprising the curable silicone composition of  claim 1 . 
     
     
       25. The personal care composition of  claim 24 , wherein the personal care composition is chosen from a cosmetic formulation, a sunscreen, a shampoo, a conditioner, a lotion, or a cream. 
     
     
       26. A method of forming a cured article comprising subjecting the composition of  claim 1  to heat and/or UV radiation conditions to effect curing of the composition. 
     
     
       27. A compound of the formula: 
       
         
           
           
               
               
           
         
         where R 2  is of the formula X—R 16 — where X is bicyclo[2.2.1]heptane or R 2  comprises a methacrylate group, and R 16  is a bond or a C1-C20 monovalent hydrocarbon radical; 
         wherein R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , and R 14  are methyl; R 5  and R 11  are phenyl; R 1  comprises a bicyclo[2.2.1]heptane group; 
         x and z are independently 1-30; 
         y and w are independently 0-30, y+w≥1; and 
         n is 1-30. 
       
     
     
       28. The compound of  claim 27 , wherein R 1  is chosen from a divalent group comprising a C4-C30 cyclic-containing hydrocarbon group chosen from a cyclobutyl group, cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a divalent group derived from 1,1-diethenyl cylcohexane; 1,3-diethenyl cylcohexane; bicyclo[2.2.1]-2,5-dienthenylheptane; 1,4-di-2-prope-1-nylcyclochexane; a spiro[5.5]-3,8-diethenylundecane; a 1,3-diethenyladamantane; a vinyl norbornene; 3,9-divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane; or pinane, bornane, norpinane, norbornane, spiro[2.2]pentane, spiro[2.3]hexane, spiro[2.4]heptane, spiro[2.5]octane, spiro[3.3]heptane, spiro[3.4]octane, spiro[3.5]nonane, spiro[4.4]nonane, spiro[4.5]decane, spiro[5.5]undecane, bicyclo[1.1.0]butane, bicyclo[2.1.0]pentane, bicyclo[2.2.0]hexane, bicyclo[3.1.0]hexane, bicyclo[3.2.0]heptane, bicyclo[3.3.0]octane, bicyclo[4.1.0]heptane, bicyclo[4.2.0]octane, bicyclo[4.3.0]nonane, bicyclo[4.4.0]decane, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, bicyclo[3.2.2]nonane, bicyclo[3.3.1]nonane, bicyclo[3.3.2]decane, bicyclo[3.3.3]undecane, an adamantyl, tricyclo[5.2.1.0 2,6 ]decane tricyclo[4.3.1.1 2,5 ]undecane rings. 
     
     
       29. The compound of  claim 27 , wherein R 2  is chosen from a C1-C20 hydrocarbon radical comprising a vinyl functional group, a monovalent C4-C20 branched hydrocarbon radical comprising a vinyl functional group, or a monovalent C4 to C30 cyclic hydrocarbon radical comprising a vinyl functional group. 
     
     
       30. The compound of  claim 27 , wherein R 2  is of the formula X—R 16 — where X is the curable functional group chosen from a vinyl group (CH 2 ═CH 2 —), an unsaturated cyclic group, an unsaturated polycyclic group, and R 16  is a bond or a monovalent hydrocarbon. 
     
     
       31. The compound of  claim 30 , wherein X is chosen from cyclopentene, cyclohexene, cyclooctene, pinene, bornene, norpinene, norbornene, spiro[2.2]pentene, spiro[2.3]hexene, spiro[2.4]heptene, spiro[2.5]octene, spiro[3.3]heptene, spiro[3.4]octene, spiro[3.5]nonene, spiro[4.4]nonene, spiro[4.5]decene, spiro[5.5]undecene, bicyclo[1.1.0]butene, bicyclo[2.1.0]pentene, bicyclo[2.2.0]hexene, bicyclo[3.1.0]hexene, bicyclo[3.2.0]heptene, bicyclo[3.3.0]octene, bicyclo[4.1.0]heptene, bicyclo[4.2.0]octene, bicyclo[4.3.0]nonene, bicyclo[4.4.0]decene, bicyclo[1.1.1]pentene, bicyclo[2.1.1]hexene, bicyclo[2.2.1]heptene, bicyclo[2.2.2]octene, bicyclo[3.1.1]heptene, bicyclo[3.2.1]octene, bicyclo[3.2.2]nonene, bicyclo[3.3.1]nonene, bicyclo[3.3.2]decene, bicyclo[3.3.3]undecene, an adamantene, tricyclo[5.2.1.0 2,6 ]decene, tricyclo[4.3.1.1 2,5 ]undecene rings, a limonene, a camphene, a limonene oxide, a vinyl cyclohexyl epoxide, a dicyclopentadiene, 5-ethylidene-2-norbornene, 2-vinyl adamantane, 2-methylene admantane, dicyclopentadiene, or (−)-beta-chamigrene, 4-vinyl cyclohexyl. 
     
     
       32. The compound of  claim 27 , wherein R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , and R 14  are methyl; R 5  and R 11  are phenyl; R 1  is comprises a bicyclo[2.2.1]heptane group, and R 2  comprises a methacrylate group. 
     
     
       33. The compound of  claim 27 , wherein the compound is of the formula: 
       
         
           
           
               
               
           
         
       
     
     
       34. The compound of  claim 27 , wherein the compound is of the formula: